3-benzylpropyl β-D-glucopyranosyluronic acid | 325962-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzylpropyl β-D-glucopyranosyluronic acid
• 英文别名: (2S,3S,4S,5R,6R)-6-(3-benzylsulfanylpropoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 325962-10-5
• 化学式: C₁₆H₂₂O₇S
• 分子量: 358.412
• InChiKey: ORAMNHSTYQVDMR-JHZZJYKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  bis[(3-bromopropylsilyl)propyl]dimethylsilane 、 3-benzylpropyl β-D-glucopyranosyluronic acid 在 sodium 作用下， 以 氨 、 四氢呋喃 为溶剂， 反应 1.0h， 以64%的产率得到
  参考文献：
  名称：

  Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent Sn2 reaction

  摘要：

  Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00247-0
• 作为产物：
  描述：

  methyl (allyl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 在 sodium hydroxide 、 偶氮二异丁腈 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.75h， 生成 3-benzylpropyl β-D-glucopyranosyluronic acid
  参考文献：
  名称：

  Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent Sn2 reaction

  摘要：

  Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00247-0

文献信息

• Introduction of monosaccharides having functional groups onto a carbosilane dendrimer: A broadly applicable one-pot reaction in liquid ammonia involving Birch reduction and subsequent Sn2 reaction
  作者：Koji Matsuoka、Hidehiro Kurosawa、Yasuaki Esumi、Daiyo Terunuma、Hiroyoshi Kuzuhara

  DOI：10.1016/s0008-6215(00)00247-0

  日期：2000.12

  Benzylthioalkyl glycosides of D-glucuronic acid, N-acetyl-D-glucosamine, and N-acetylneuraminic acid (common monosaccharide constituents of natural oligosaccharide chains) have been prepared as sulfide precursors for the carbohydrate coating of dendric carbosilane cores and used in a generally applicable one-pot reaction (Birch reduction in liquid ammonia and subsequent SN2 reaction) to generate a thioether linkage between the monosaccharide moieties and a carbosilane dendrimer. The dendrimers were uniformly functionalized with the monosaccharides in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.